5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole → 6-(Ethyl(2-hydroxyethyl)amino)-5-(1H-pyrazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide
Reaction equation
Br[C:2]1[C:3]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].CC1(C)C(C)(C)OB([C:36]2[N:40](COCC[Si](C)(C)C)[N:39]=[CH:38][CH:37]=2)O1>>[CH2:26]([N:22]([CH2:23][CH2:24][OH:25])[C:3]1[C:2]([C:36]2[NH:40][N:39]=[CH:38][CH:37]=2)=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])=[CH:5][N:4]=1)[CH3:27]Participants
3
Procedure
The title compound was prepared in an analogous fashion to that described in Example 19 using 5-bromo-6-(ethyl(2-hydroxyethyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 21.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole to afford a yellow wax UPLC-MS (Condition 3) tR=0.97 min, m/z=436.2 [M+H]+, m/z=434.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.93 (t, J=6.97 Hz, 3H) 3.26 (br. s, 2H) 3.36-3.44 (m, 2H) 3.44-3.52 (m, 2H) 4.59 (br. s, 1H) 6.53 (d, J=1.96 Hz, 1H) 7.34 (d, J=8.31 Hz, 2H) 7.80 (br. s, 1H) 7.84-7.90 (m, 2H) 8.13 (s, 1H) 8.71 (d, J=1.96 Hz, 1H) 10.28 (s, 1H) 12.94 (br. s, 1H).
Workup
- customto afford a yellow wax UPLC-MS (Condition 3) tR=0.97 min, m/z=436.2 [M+H]+, m/z=434.3 [M−H]−
Sources & evidence
- ORD record
- ord-4b787b3aad974797b0e965d23360c282
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340537B2
Reaction notes
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